i started out with a cheap *** chinese cutter i got on ebay for $500 with software back in 2006. I Started selling decals as a hobby to friends and on ebay. Purchased a heat press then started cutting heat transferable film and making hoodies, hats, shirts etc. Made lots of money over the years, saved up and in 2010 got a nice new mutoh printer, a graphtec cutter, flexi sign pro, and laminator. Now I run a successful business.
I didnt know a damn thing about how to design, or run sign making software, AI, Photoshop etc when i started in 2006. You will learn as you go.
The only thing you really do need to worry about is buying a cheap chinese cutter and it breaks down or other issues with it. I got lucky with mine, and it still works today (my fiancee uses it) with the exception of the manual feed forward button not working.
There really is a night and day difference between a chinese cutter and a brand name one. When i got my graphtec i was amazed at how fast, accurate, and quiet it is.
Anyways, I do suggest you get a used brand name cutter. Because the chances of getting a chinese cutter that will in some way break on you are pretty high.